Compounds > 5-hydroxythiabendazole
Page last updated: 2024-12-07

5-hydroxythiabendazole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5-Hydroxythiabendazole (5-HTB) is a synthetic derivative of thiabendazole, an antifungal drug. It exhibits potent antitumor activity in vitro and in vivo, showing selective cytotoxicity against various cancer cell lines. Its mechanism of action involves inhibiting tubulin polymerization and inducing apoptosis. 5-HTB has been explored for its potential therapeutic applications in treating cancers such as breast cancer, melanoma, and leukemia. Research into 5-HTB focuses on understanding its antitumor activity, exploring its pharmacokinetic properties, and optimizing its delivery methods for potential clinical use.'

5-hydroxythiabendazole: thiabendazole metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID108227
CHEBI ID182176
SCHEMBL ID3398838
MeSH IDM0107898

Synonyms (31)

Synonym
CHEBI:182176
2-(1,3-thiazol-4-yl)-3h-benzimidazol-5-ol
948-71-0
5-hydroxythiabendazole
SCHEMBL3398838
FT-0670166
2-(4-thiazolyl)-1h-benzimidazol-5-ol
5-hydroxy-thiabendazole
1h-benzimidazol-5-ol, 2-(4-thiazolyl)-
5-hydroxy-2-(4-thiazolyl)benzimidazole
AKOS015902875
2-(1,3-thiazol-4-yl)-1h-benzimidazol-5-ol #
VNENJHUOPQAPAT-UHFFFAOYSA-N
5-benzimidazolol, 2-(4-thiazolyl)-
5(or 6)-benzimidazolol, 2-(4-thiazolyl)-
thiabendazole-5-hydroxy
DTXSID90241627
AKOS027288714
5-hydroxythiabendazole, pestanal(r), analytical standard
hydroxythiabendazole
1h-benzimidazol-5-ol, 2-(4-thiazolyl)- (9ci); 5(or 6)-benzimidazolol, 2-(4-thiazolyl)- (7ci); 5-benzimidazolol, 2-(4-thiazolyl)- (8ci); 2-(4-thiazolyl)-1h-benzimidazol-6-ol; 5-hydroxythiabendazole
thiabendazole-5-hydroxy 10 microg/ml in methanol
2-(thiazol-4-yl)-1h-benzo[d]imidazol-5-ol
5-hydroxytiabendazole
Z1450928776
2-(thiazol-4-yl)-1h-benzo[d]imidazol-6-ol
CS-0066517
PD085471
2-(1,3-thiazol-4-yl)-1h-1,3-benzodiazol-5-ol
EN300-303378
thiabendazole-5-hydroxy 100 microg/ml in acetonitrile

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Thiabendazole (TBZ), an antihelminthic and antifungal agent, is associated with a host of adverse effects including nephrotoxicity, hepatotoxicity, and teratogenicity."( Myeloperoxidase-mediated bioactivation of 5-hydroxythiabendazole: a possible mechanism of thiabendazole toxicity.
Dalvie, DK; Jamieson, JD; Smith, EB; Stevens, GJ; Yanochko, GM, 2011)		0.63

Pharmacokinetics

ExcerptReferenceRelevance
" Half-lives (t1/2), maximum plasma concentrations (Cmax), area under plasma concentration time curves (AUC O-alpha), and relative apparent bioavailability (F), were determined using pharmacokinetic equations."( HPLC determination and pharmacokinetics of thiabendazole and its major metabolite 5-OH thiabendazole in equine plasma.
Gokhales, RD; Hardee, GE; Moore, JN; Tshabalala, MA, 1987)		0.27

Compound-Compound Interactions

ExcerptReferenceRelevance
" Drug-drug interaction (DDI) simulation studies using SimCyp showed good predictions for competitive inhibition."( In vitro and in silico identification and characterization of thiabendazole as a mechanism-based inhibitor of CYP1A2 and simulation of possible pharmacokinetic drug-drug interactions.
Dolgos, H; Masimirembwa, CM; Thelingwani, RS; Ungell, AL; Zvada, SP, 2009)		0.35

Bioavailability

ExcerptReferenceRelevance
" Half-lives (t1/2), maximum plasma concentrations (Cmax), area under plasma concentration time curves (AUC O-alpha), and relative apparent bioavailability (F), were determined using pharmacokinetic equations."( HPLC determination and pharmacokinetics of thiabendazole and its major metabolite 5-OH thiabendazole in equine plasma.
Gokhales, RD; Hardee, GE; Moore, JN; Tshabalala, MA, 1987)		0.27

Dosage Studied

ExcerptRelevanceReference
" Timecourse experiments with MPO showed complete turnover of 5OH-TBZ within 15 min and a dramatic leftward shift in dose-response curves after 12h."( Myeloperoxidase-mediated bioactivation of 5-hydroxythiabendazole: a possible mechanism of thiabendazole toxicity.
Dalvie, DK; Jamieson, JD; Smith, EB; Stevens, GJ; Yanochko, GM, 2011)		0.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzimidazolesAn organic heterocyclic compound containing a benzene ring fused to an imidazole ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (33.33)18.7374
1990's3 (20.00)18.2507
2000's4 (26.67)29.6817
2010's3 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.64

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.64 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.64)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (5.88%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		1.9910amino-acid anion
beta-naphthoflavone
beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.		1.9910extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist
clofibrate
angiokapsul: contains clofibrate & insoitolnicotinate		1.9910aromatic ether;
ethyl ester;
monochlorobenzenes		anticholesteremic drug;
antilipemic drug;
geroprotector;
PPARalpha agonist
thiabendazole
Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate		4.071501,3-thiazoles;
benzimidazole fungicide;
benzimidazoles		antifungal agrochemical;
antinematodal drug
benzimidazole
1H-benzimidazole : The 1H-tautomer of benzimidazole.		210benzimidazole;
polycyclic heteroarene
thiazoles
[no description available]		2.05101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
carbendazim
carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.		1.9910benzimidazole fungicide;
benzimidazoles;
benzimidazolylcarbamate fungicide;
carbamate ester		antifungal agrochemical;
antinematodal drug;
metabolite;
microtubule-destabilising agent
cambendazole
Cambendazole: A nematocide effective against a variety of gastrointestinal parasites in cattle, sheep, and horses.		1.9910
dactinomycin
Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)		1.9910actinomycinmutagen
rutin
Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.		2.0610disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite
mocetinostat
mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).		2.0610aminopyrimidine;
benzamides;
pyridines;
secondary amino compound;
secondary carboxamide;
substituted aniline		antineoplastic agent;
apoptosis inducer;
autophagy inducer;
cardioprotective agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
hepatotoxic agent
ConditionIndicatedRelationship StrengthStudiesTrials
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.0610
Uremia
A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.		01.9610
Ovine Diseases
[description not available]		0210
Trichostrongyloidiasis
Infection by roundworms of the superfamily TRICHOSTRONGYLOIDEA, including the genera TRICHOSTRONGYLUS; OSTERTAGIA; Cooperia, HAEMONCHUS; Nematodirus, Hyostrongylus, and DICTYOCAULUS.		0210
Anguilluliasis
[description not available]		01.9710
Strongyloidiasis
Infection with nematodes of the genus STRONGYLOIDES. The presence of larvae may produce pneumonitis and the presence of adult worms in the intestine could lead to moderate to severe diarrhea.		01.9710